288 Middlesex Avenue, Chester, CT 06412 (MLS # 24166793)


Price $3,150,000
Status Active
Beds 4
Baths 5 Baths
Home size 4,626 sqft
Lot Size 2.65 ac
Days on Market 126
Set along a coveted stretch of the Connecticut River, this stunning, turnkey waterfront compound offers a rare convergence of privacy, protected views, and deep water access-just over one mile from the heart of Chester Village. Encompassing 2.65 acres with 285 feet of direct river frontage, the property unfolds as a true waterfront retreat. Manicured grounds lead seamlessly from the residence and terrace to a deepwater dock designed for serious boating enthusiasts, and onward to a beach-creating an immersive riverfront experience rarely found in the CT River Valley. Rooted in historic design and masterfully renovated in 2010, the residence reflects timeless New England architecture while incorporating modern livability. The result is a home that feels both enduring and refined. A standout feature for collector/hobbyists are six garage bays, offering exceptional space for auto enthusiasts, boating and recreational storage. Designed to accommodate a range of lifestyles, this offering is equally compelling as a luxury weekend retreat or a multi-generational compound, with space and setting that invite both privacy and gathering. Despite its seclusion, the estate remains connected to the vibrant charm of Chester Village. Adding to the setting's unique appeal, the seasonal Connecticut Valley Railroad introduces a nostalgic dimension, reflecting the rich area history. A rare offering where protected waterfront, architectural integrity and lifestyle converge. Welcome to East View.
Property Type(s): Single Family
Last Updated 4/13/2026 Year Built 1800
Garage Spaces 6.0 County Middlesex

SCHOOLS

Elementary School Chester
Jr. High School Winthrop
High School Valley

Additional Details

AIR Central Air
AIR CONDITIONING Yes
APPLIANCES Convection Oven, Dishwasher, Dryer, Gas Range, Microwave, Range Hood, Washer, Wine Cooler
BASEMENT Concrete, Full, Partially Finished, Storage Space, Yes
CONSTRUCTION Cedar, Frame, Shake Siding
EXTERIOR Balcony, Dock
FIREPLACE Yes
GARAGE Attached Garage, Yes
HEAT Forced Air, Oil
INTERIOR Entrance Foyer, Sauna, Sound System
LOT 2.65 acre(s)
LOT DESCRIPTION Waterfront
PARKING Garage Door Opener, Attached
SEWER Septic Tank
STYLE Colonial
TAXES 24724
UTILITIES Underground Utilities
VIEW Yes
VIEW DESCRIPTION Water
WATER Well
WATERFRONT Yes
WATERFRONT DESCRIPTION River Front
ZONING R-2

Location

 

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